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Paper | Special issue | Vol 82, No. 1, 2010, pp.663-687
Published online, 8th July, 2010
DOI: 10.3987/COM-10-S(E)42
Synthesis and Anti-HIV Activity of New 3’-O-Phosphonomethyl Nucleosides

Michal Cesnek and Piet Herdewijn*

*K.U. Leuven, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium

Abstract

The synthesis of 4’(S)-ethynyl-2’-deoxythreosyl and β-D-galactofuranose nucleosides starting from D-galactose is described. The nucleobase is introduced using Vorbruggen glycosylation. The 4’(S)-ethynyl derivatives are obtained by selective oxidation of vicinal diol to the aldehyde and subsequent Bestmann modification of Seyferth-Gilbert homologation. All compounds were evaluated for activity against HIV (MT4 cells), RSV (Hep2 cells) and HCV (HCV replicon cells), however, none of these compounds demonstrate biological activity.